I’d start with 2 (loaded) questions first:
- Can she and I together get this start-up to initial traction and beyond in 2–3 years? For real?
- Do the two of us have the right combination of skills and background to pull it off? If not, who do can we bring onto the team now?
Everything else sort of comes second. Yes, it would be great if one of you was strong in sales and the other in technology. But maybe you both are great engineers. Or maybe you both are great in sales, and you recruit an amazing CTO. There are many ways to the top of a mountain.
- Not being committed enough. Years, not months, upfront.
- Not being aligned.
- Not being able to pull it off.
- Not being able to build the right team.
These are the things that stop wannapreneurs from becoming true entrepreneurs.